Doug's First Time
by Jimmy Lee
Copyright© 2025 by Jimmy Lee
Coming of Age Sex Story: Bud and I finally get Doug laid.
Caution: This Coming of Age Sex Story contains strong sexual content, including mt/ft Consensual Heterosexual Fiction First Oral Sex Size .
“God damn! You ain’t sticking that boloney roll in me!” That ended Doug’s and my chances of getting any pussy that night.
There were three of us: me, Doug, and Bud. I lived about 25 miles out in the country and had a car. Bud lived in the city’s West End, the “baddest part of town”, as a Jim Croce song phrased it. Doug lived in a small town about 15 miles north of the city. We’d all met via CB radios and had become fast friends. Once we’d thought of calling ourselves “the Three Musketeers”, but none of us liked that worn-out reference so it died as quickly as it came up.
Doug was big, 6’ 3” with a lean, muscular body and a baby face which the girls all thought was cute, but killed any attraction he might have held. I’d overheard them talking about him saying that he was cute and had an awesome body, but he just didn’t “do it” for them.
Bud and I had girlfriends and got laid at least every weekend, usually on double dates in my car. Doug was still a virgin, so Bud and I made it our mission to rectify that aberration. One of those attempts was tonight. Bud had set Doug up with the West End’s roundest-heeled girl. She was pretty, in a slutty way; the kind of girl you’d see walking down the street and wonder how much she charged or figured she would put out to pretty much anyone swinging meat between his legs.
We were in the back row of the local fuck-in, a drive-in movie theater where the roaming security guards ignored what went on in the furthest and darkest three rows. Marsha, my girlfriend, was ready, my rubber was on, and I was about to slip it in when Miss Slutty freaked. I raised up and looked over the back of the front seat. She had her hands on his chest and one foot on his hips pushing him away. Holy fuck! I’d seen him soft a few times and knew he was large, but sweet Jesus! That thing had to take enough blood to make him lightheaded. I wondered why he didn’t pass out.
“You can eat me, and I’ll jerk you off, but there’s no way you’re fucking me. That fucking thing will kill me.”
Being so close to something he’d so long been denied brought Doug’s frustration to a head. He grabbed her legs by the ankles, pushing them back to her shoulders and began stabbing at her with that monster. “Come on, damn it, you’ll like it once it’s in.” She was twisting her body to dodge him, and I momentarily had a vision of trying to thread a moving needle with a rope.
“Doug, no. Dude, not in my car. Settle down.” I reached back and punched him in the ribs, not hard, but not gentle either, just to get his attention. He stopped thrusting, his head bowed, and he relaxed his grip on her legs.
Sitting back on the driver’s side of the rear seat, he looked much like a scolded child. “I’m sorry. I don’t mean to hurt you.” God, he sounded dejected as he began straightening his clothes.
“That’s okay, honey,” Miss Slutty said. “I know how men are. Want me to jerk you off?”
“Nah. Fuck it.” With that Doug got out and walked away.
“Where’s he going? Is he going to be okay,” she asked us.
“He’s probably going home, and he’ll be fine,” I replied. Knowing him, he’d spend the rest of the night walking the 15-plus miles. “Y’all got any interest in the movies?” They didn’t, so we headed out to the Sambo’s for burgers and fries. It was on the route out of town to Doug’s home, but I didn’t see him. After dropping the other girl off we quickly fucked in the parking lot of Marsha’s apartment (she lived with her Mom). I was glad for some release because my balls were aching. I bet Doug’s were, too. He should have gone for the handjob. At least he would have had ONE experience cumming from the attentions of a live woman. I wondered if she would have swallowed his cum. Damn, I was sure he’d missed out, even without getting it wet.
Bud and I ramped up our efforts to get Doug laid. One afternoon at the Burger King I ran into Frances, someone I’d gone to school with. High school cheerleader turned hooker. She and I had never gotten along. I was something of an outsider in that rural Southern redneck area because I wasn’t into football and wore my hair longer than some girls there. I’d paid her pimp $50 to fuck her several months ago. She’d thought it was her regular money plus the fifty. She was pissed to have to fuck me, and even more when she learned how cheap he’d sold her to me. I sat down at her table uninvited, told her about Doug’s problem, and asked if she had any suggestions, somewhat hoping she’d offer to solve the issue herself.
“Another freebie, asshole?” I just grinned and waited. “I think I may know someone,” she said through a mouthful of Whopper. “She’s not pro, but she has helped me and some other girls sometimes with parties.” She wrote “Lorie” and a phone number on a napkin. “Just tell her I sent you. I’ve heard her mention she’s taken some horse cocks before.” Not actual horse cocks, just big human dicks.
I gave Lorie a call and after chatting we set up a double date with Doug for the next Saturday. “If it’s the challenge you make it sound like, I won’t even charge,” she said with a giggle. I called Doug and told him I had a date set up, that she was pretty much a sure-fire thing. I didn’t mention about how I’d found her or her comment about charging. I figured he would do better thinking the girl actually wanted him rather than seeing him as a client. His response was in the “Yeah, whatever” category.
Saturday came and we all met at the Krystal parking lot. That was Lorie’s suggestion, I suspect for her own safety. The Krystal was on the Atlanta Highway, one of the turnaround points for the weekend cruisers. They always had an off-duty cop for a security guard. Instead of going straight to the fuck-in, Lorie suggested dinner first, so we headed to the Howard-Johnson’s restaurant on the Southern Bypass.
She was a few years older than us, but that seemed to be even more because of how she handled herself rather than her looks. She had wide hips, narrow waist, and a nice set of boobs that stressed the blouse hiding them. A miniskirt showed her long legs off to their best advantage while giving promise of what was hiding just above it. This woman knew how to dress to pop a pecker. As we stood in the parking lot Marsha slipped her thumb into the waist of my pants and pulled me tight to her. I silently chuckled at her possessiveness.
At the Ho-Jo’s, Lorie wanted a booth, and insisted the girls sit on one side and the boys on the other. Okay, whatever. We ordered and chatted until the food came. Lorie seemed particularly interested in Doug, and Doug was obviously loving the female attention. It was looking pretty certain that he’d get an opportunity for pussy and I wondered how that would play out.
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